Subscribe to RSS
Synthesis of (±)-Hibiscone C
Total Synthesis of Hibiscone C (Gmelofuran).
J. Am. Chem. Soc. 1982;
Key words(±)-hibiscone C - furanosesquiterpenoid - Stork–Danheiser transposition - [2+2] cycloaddition - Paal–Knorr furan synthesis
In 1982, Koft and Smith reported the first total synthesis of (±)-hibiscone C, a furanosesquiterpenoid which was isolated from the heart wood of Hibiscus elatus. The synthesis featured the first example of a photochemical intramolecular enone–alkyne cycloaddition.
Alkylation of A with B followed by reductive Stork–Danheiser transposition afforded C. Irradiation of C gave an inconsequential mixture of D and E, which was converted into G via ozonolysis and Paal–Knorr furan synthesis. Allylic oxidation followed by α-methylation yielded (±)-hibiscone C.
17 September 2020 (online)
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany